141-30-0

Basic information

• Product Name: 3,6-Dichloropyridazine
• Synonyms: 3,6-Dichloro Pyridine;Pyridazine,3,6-dichloro-;3,6-Dichloropyridazine,97%;3,6-Dichloropyridazi;6-Dichloropyridazine;3,6-Dichloropyridazine, 97% 100GR;3,6-Dichloropyridazine, 98%+;3,6-dichloro-pyridazin
• CAS NO: 141-30-0
• Molecular Formula: C₄H₂Cl₂N₂
• Molecular Weight: 148.98
• EINECS: 205-478-6
• Product Categories: Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridazines;PyridazinesHeterocyclic Building Blocks;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;alkyl chloride;Pesticides intermediate
• Mol File: 141-30-0.mol

Chemical Properties

• Melting Point: 65-69 °C(lit.)
• Boiling Point: 244.21°C (rough estimate)
• Flash Point: 147.9 °C
• Appearance: White to almost white/Crystalline Powder
• Density: 1.6445 (rough estimate)
• Vapor Pressure: 0.00782mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: Refrigerator
• Solubility: 0.0012g/l
• PKA: -1.18±0.10(Predicted)
• Water Solubility: Soluble in chloroform. Insoluble in water.
• BRN: 111151
• CAS DataBase Reference: 3,6-Dichloropyridazine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Dichloropyridazine(141-30-0)
• EPA Substance Registry System: 3,6-Dichloropyridazine(141-30-0)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-25-20
• Safety Statements: 26-37/39-45-22-36/39-36
• RIDADR: 2811
• WGK Germany: 3
• RTECS: UR5886250
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 141-30-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,6-Dichloropyridazine is used as a synthetic intermediate for the creation of various active pharmaceutical ingredients. Its chemical properties make it a valuable compound in the development of new drugs and therapies.
Used in Chemical Synthesis:
3,6-Dichloropyridazine is utilized in the preparation of alfa-(halohetaroyl)-2-azahetarylacetonitriles, which are important compounds in the field of chemical synthesis. This application highlights its versatility and importance in the synthesis of complex molecules for various industries.

InChI:InChI=1/C4H2Cl2N2/c5-3-1-2-4(6)8-7-3/h1-2H

Upstream product

• 123-33-1 Maleic hydrazide 
• 19064-67-6 6-chloro-2H-pyridazin-3-one 
• 123-33-1 3,6-dihydroxypyridazine 
• 25974-26-9 3,6-dichloropyridazine-1-oxide 
• 42413-70-7 pyridazine-3,6-dione 
• 123-33-1 6-hydroxy-3-pyridazinone 
• 14628-35-4 maleic dihydrazide 
• 75-20-7 calcium carbide 
• 106131-61-7 3,6-dichloro-1,2,4,5-tetrazine 
• 935-04-6 benzyl vinyl ether 
• 5469-69-2 6-chloro-pyridazin-3-ylamine 
• 71-43-2 benzene 

Downstream Products

• 1722-11-8 3-chloro-6-(piperidin-1-yl)pyridazine 
• 17321-20-9 3-chloro-6-(ethyloxy)pyridazine 
• 98949-29-2 3-chloro-6-(4-chloro-phenylsulfanyl)-pyridazine 
• 101081-65-6 3,6-bis-(4-chloro-phenylsulfanyl)-pyridazine 
• 1722-10-7 3-chloro-6-methoxypyridazine 
• 4603-59-2 3,6-dimethoxypyridazine 
• 37813-54-0 3,6-bis(methylthio)pyridazine 
• 10340-55-3 3,6-diphenoxypyridazine 
• 64383-28-4 3-chloro-6-phenylsulfanyl-pyridazine 
• 19064-67-6 6-chloro-2H-pyridazin-3-one 
• 80-32-0 sulfachloropyridazine 
• 29604-73-7 3,6-Bis-(dimethylamino)-pyridazin 
• 289-80-5 1,2-diazine 
• 5469-69-2 6-chloro-pyridazin-3-ylamine 

Relevant articles and documents

Intermolecular contacts in the crystal structures of specifically varied halogen and protonic group substituted azines

A series of azines featuring differently halogen and protic group substituted pyridine, pyrimidine and pyridazine compounds have been synthesized and studied in terms of their crystal structures in order to develop a better understanding of the links between structural conditions and molecular packing behavior. Complemented by the structure results of related compounds known from the literature, intermolecular contact relationships connected to the present substance types were found, having potential use in future crystal engineering of similar compounds. This primarily involves the formation of N?I contacts aside from specific halogen?halogen and hydrogen bond type interactions.

One-Pot and Two-Chamber Methodologies for Using Acetylene Surrogates in the Synthesis of Pyridazines and Their D-Labeled Derivatives

Acetylene surrogates are efficient tools in modern organic chemistry with largely unexplored potential in the construction of heterocyclic cores. Two novel synthetic paths to 3,6-disubstituted pyridazines were proposed using readily available acetylene surrogates through flexible C2 unit installation procedures in a common reaction space mode (one-pot) and distributed reaction space mode (two-chamber): (1) an interaction of 1,2,4,5-tetrazine and its acceptor-functionalized derivatives with a CaC2?H2O mixture performed in a two-chamber reactor led to the corresponding pyridazines in quantitative yields; (2) [4+2] cycloaddition of 1,2,4,5-tetrazines to benzyl vinyl ether can be considered a universal synthetic path to a wide range of pyridazines. Replacing water with D2O and vinyl ether with its trideuterated analog in the developed procedures, a range of 4,5-dideuteropyridazines of 95–99% deuteration degree was synthesized for the first time. Quantum chemical modeling allowed to quantify the substituent effect in both synthetic pathways.

Polymorph-specific chlorination of maleic-hydrazide

The reaction of chlorination of maleic-hydrazide (1) with POC13 is specific to the substrate polymorph. Chlorination of either the triclinic polymorph of maleic-hydrazide (1), denoted MH1, or the monoclinic polymorph MH2 leads to a single product of 3,6-dichloropyridazine (2), while chlorination of the monoclinic polymorph MH3 under the same conditions results in two products: 3,6-dichloropyridazine (2) and 6-chloro-3-pyridazinone (3). The structural differences between polymorphs and their topochemical chlorination in phosphorus oxychloride are discussed. The crystal structure of 6-chloro-3-pyridazinone (3) monohydrate, determined in this study by X-ray diffraction, is built of ribbons of hydrogen-bonded 3 and water molecules. It has been established that the chlorination of ground crystals of polymorph MH3 yields exclusively the dichloropyridazine, which suggests that the crystal habit of MH3, the size of crystallites and the lower solubility of MH3 than MH1 and MH2 are the main reasons for the different course of the reaction.

Synthesis and herbicidal evaluation of 3-N-substituted amino-6-benzyloxypyridazine derivatives

A variety of 3-N-substituted amino-6-benzyloxypyridazine derivatives were designed and synthesized in satisfactory yields. Their structures were confirmed by IR, 1H-NMR, and elemental analysis; compound 5j was further determined by X-ray diffraction crystallography. Their herbicidal activities were evaluated through barnyard grass and rape cup tests in laboratory bioassays. Most of the title compounds 5 displayed moderate herbicidal activities against the dicotyledonous plant Brassica campestris L. The most active compounds in the laboratory were also evaluated in the greenhouse.

Pyridazine N-Oxides as Photoactivatable Surrogates for Reactive Oxygen Species

A method for the photoinduced evolution of atomic oxygen from pyridazine N-oxides was developed. This underexplored oxygen allotrope mediates arene C-H oxidation within complex, polyfunctional molecules. A water-soluble pyridazine N-oxide was also developed and shown to promote photoinduced DNA cleavage in aqueous solution. Taken together, these studies highlight the utility of pyridazine N-oxides as photoactivatable O(3P) precursors for applications in organic synthesis and chemical biology.

Deaminative chlorination of aminoheterocycles

Selective modification of heteroatom-containing aromatic structures is in high demand as it permits rapid evaluation of molecular complexity in advanced intermediates. Inspired by the selectivity of deaminases in nature, herein we present a simple methodology that enables the NH2 groups in aminoheterocycles to be conceived as masked modification handles. With the aid of a simple pyrylium reagent and a cheap chloride source, C(sp2)?NH2 can be converted into C(sp2)?Cl bonds. The method is characterized by its wide functional group tolerance and substrate scope, allowing the modification of >20 different classes of heteroaromatic motifs (five- and six-membered heterocycles), bearing numerous sensitive motifs. The facile conversion of NH2 into Cl in a late-stage fashion enables practitioners to apply Sandmeyer- and Vilsmeier-type transforms without the burden of explosive and unsafe diazonium salts, stoichiometric transition metals or highly oxidizing and unselective chlorinating agents. [Figure not available: see fulltext.]

Preparation method of 3, 6-dichloropyridazine

The invention belongs to the technical field of medicines, and particularly relates to a preparation method of 3, 6-dichloropyridazine. The preparation method comprises the following steps: carrying out chlorination reaction on 3, 6-dihydroxypyridazine and N-chlorosuccinimide to generate 3, 6-dichloropyridazine; the chlorination reaction route is as follows: the method solves the technical problems of large environmental pollution, high process risk and high cost due to the adoption of the traditional chlorinating agent in the existing 3, 6-dichloropyridazine preparation method.

Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis

The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.

Preparation method of chloro-substituted polyhydroxy aza-aromatic ring compound (by machine translation)

The invention discloses a preparation method, namely BTC and SOCl, of a chloropolyhydroxyl aza heteroaromatic ring compound as a raw material with a polyhydroxy aza heteroaromatic ring compound as a raw material, and a preparation method thereof. 2 As the double chlorination reagent, a chloropolyhydroxyl aza-aromatic ring compound is produced by chlorination reaction with 4 - dimethylaminopyridine (DMAP) as a catalyst at room temperature to reflux temperature of the reaction, as a catalyst. BTC TC TC TC2 /DMDMAP chlorination system has high efficiency, high selectivity and chlorine substitution on a polyhydroxy nitrogen heterocyclic compound; the system can replace POCl3 , The production of phosphorus-containing wastewater is avoided. Using BTC as a chlorination reagent, the reaction by-product was HCl and CO. 2 . From the aspects of industrial wastewater treatment, environmental protection and the like, the advantages thereof are obvious; SOCl is distilled off after the reaction is ended. 2 The quantity is almost no loss, can be used repeatedly, and reduces the process cost. (by machine translation)

AMINOIMIDAZOPYRIDINES AS KINASE INHIBITORS

Compounds having formula (I), and enantiomers, and diastereomers, stereoisomers, pharmaceutically-acceptable salts thereof, (I) are useful as kinase modulators, including RIPK1 modulation. All the variables are as defined herein.